Triethylamine → HCID 73291822, compound

HRID 530467Notes

Reaction equation

CCN(CC)CC.O[C@@H:9]([CH3:26])[C@@H:10]([NH:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:16])[C:11]([OH:13])=[O:12].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH2:18]([O:17][C:15](=[O:16])[NH:14][C@H:10]1[C:11](=[O:13])[O:12][C@H:9]1[CH3:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

In a four-necked round bottom flask, Et3N (1.5 mL, 10.9 mmol) was added to a solution of (2R,3S)-3-hydroxy-2-{[(octyloxy)carbonyl]amino}butanoic acid (1 g, 3.63 mmol) in dry CH2Cl2 (40 mL) under argon. After cooling at 0° C., HBTU (2.07 g, 5.45 mmol) was added and the mixture stirred 3 h at 0° C., then 3.5 h at rt. The obtained solid was filtered-off and the solvent removed under vacuum. The crude was purified by typical silica gel column chromatography, eluting with Cy/AcOEt (from 95:5 to 60:40). The resulting white solid (ca. 0.19 g) was further triturated with cyclohexane, to afford a pure compound (0.165 g, 18%) as white solid. MS (ESI) m/z: 256.31 [M−H]−. FTIR (cm−1): 3326, 2958, 2924, 2856, 1857, 1692, 1547, 1333, 1270, 1087, 1025, 845. 1H NMR (CDCl3): δ 0.87-0.90 (t, 3H); 1.28-1.36 (m, 10H); 1.47 (t, 3H); 1.59-1.66 (m, 2H); 4.06-4.15 (m, 2H); 4.84-4.91 (m, 1H); 5.38-5.48 (m, 2H).

Workup

custom3.5 h
customat rt
customthe solvent removed under vacuum
customThe crude was purified by typical silica gel column chromatography
washeluting with Cy/AcOEt (from 95:5 to 60:40)
customThe resulting white solid (ca. 0.19 g) was further triturated with cyclohexane

Sources & evidence

ORD record: ord-c18284649d584560aac03ebd73eed86c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353075B2

Reaction notes

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